The Player's Box – Episode 28: Dubai Recap & Olympic Memories

Released: February 24, 2026
Hosts: Madison Keys, Jessica Pegula, Jennifer Brady, Desirae Krawczyk

Episode Overview

In this lively episode, the Player’s Box crew—Madison Keys, Jessica Pegula, Jennifer Brady, and Desirae Krawczyk—recap their experiences at the recent Dubai tournament, share behind-the-scenes stories (with plenty of laughs), and swap Olympic memories from across multiple Games. The group navigates tennis travels, birthday mishaps, Photoshop fails, and insights into both the highs and quirks of being a pro athlete.

Key Topics & Discussions

[01:11] Dubai Title Recap & Birthday Shenanigans

• Jessica Pegula’s 10th Title: Jess shares the story of her singles win in Dubai, touching on the motivation behind her travel (“didn’t want to take another zero on my ranking”), her tough semifinal comeback against Amanda, and the rare “perfect” final performance.

  • Quote – Jessica Pegula (01:43):
    “I had a really tough match with Amanda in the semis...I felt like the final I just played like, kind of perfect. It was just one of those where everything just went my way.”

• Nolsey’s Phone Incident: Amid post-match celebrations, Pegula finds her coach “on his phone” during her finale hug (“I was like, hello?”), creating a viral meme among her team and fans.

  • Quote – Jessica Pegula (02:44):
    “I, like, ran over quick...and he was just, like, on his phone...he told me he was sending the match point video to other people!”

• Birthday Plans & Overlooked Celebrations: The group teases Jess about her upcoming birthday, only for Maddie to realize her own birthday was ignored during the last episode.

  • Memorable Moment (06:01):
    Madison: “We filmed at the exact same time last week, and my birthday was going down, and no one even mentioned it, so I’m a little salty.” Jessica: “That’s an unforced error on us. On all of us, on our team.”

[04:01] Unforced Errors of the Week

A recurring fan-favorite segment where the hosts share personal mishaps:

• Jenny’s Uber & Car Fiascos: An Uber driver assumes Jenny is “just playing tennis for fun,” and then Jenny exits from the wrong gate at the Austin venue.
• Maddie’s Birthday Snub: The forgotten birthday gets an airing.
• Jess’s “Snatched Waist” Photoshop Fail: The WTA’s social team mistakenly Photoshops Jessica’s waist and arm to cartoonish proportions in a finals promo—spawning social media hilarity.
  • Quote – Jessica Pegula (08:03):
    “It looked like they Photoshopped my waist to, like, in completely unattainable...Kim Kardashian waist size. As Maddie described it, perfectly, ‘Mrs. Incredible.’...It didn’t look real.”
• Des gets sick on her flight home (“unforced error” reluctantly accepted).

[17:32] Dubai Tournament Withdrawals & Tour Scheduling

• Pegula and Keys unpack the surge of late withdrawals—11 WD’s and multiple retirements—in Dubai.
  • Draw remains highly competitive:
    Jenny: “Look at the final. Look at the semi...The level was insane.”
• Calendar Compression: Complaints about the relentless pace—multiple 500s and 1000s, plus a Slam, all before Miami—with minimal off-season rest.
  • Quote – Madison Keys (19:45):
    “A lot of people are constantly trying to...manage injuries and then you just have weeks where sometimes you can't.”

[21:47] Dubai Doubles Drama & New Partnerships

• Desirae’s New Doubs Partner: Des teams with Luda Kichenok, and together they survive a nail-biting tiebreak with multiple match points.
• Jess Back in Doubles: Pegula and Krawczyk discuss doubles scheduling and Jess’s close defeat (“We had three match points and they won the tournament, so we basically won doubles, clearly”).
• Jenny’s Austin Comeback: Highlights from Brady’s Qualies match in Austin; she describes center court play and tough three-set loss—sums up with “You live and learn. You win or you learn.”

[28:10] Olympic Memories: Golds, Losses, and Village Life

Major Olympic Moments by Each Host

• Jessica Pegula:

  • Recalls “walking in the tunnel behind men’s basketball” at Tokyo and the electric (and fickle) French crowds at Chatrier, Paris:
    Quote (30:15):
    “They’d be cheering for me, and then I’d...bounce my racket, and then they’d start booing me, and then they’d,I’d hit a winner, and then they cheer for me again. It was just...chaos.”

• Desirae Krawczyk:

  • Highlights the “torrential rain” and boat ride during the opening ceremony in Paris, taking a selfie with LeBron James.
  • “Olympic debut” moments, village pin trading adventures.

• Jennifer Brady:

  • Biggest memory: Spotting Yao Ming at Tokyo, asking for a picture, and being turned down (“No photos”).
  • Playful: “The guy is massive!...He was like, no, no photos...Oh, okay.”

• Madison Keys:

  • 2016 Rio heartbreak: Finished 4th, saw teammates win medals, got handed only a paper certificate.
    Quote (35:36):
    “I was so upset, couldn’t even look at it... I would have rather received nothing than a piece of paper.”

Village Life & Pin Trading (38:12)

• Pegula:
  “You can never replicate...all these countries, their own buildings, flags...meeting them, collecting trading pins...so unique.”
• Krawczyk:
  "You try to be cool but also...I think we saw Simone Biles. I was like, oh my god, that's Simone."
• The legendary pin dealer:
  Des & Jenny detail Team USA captain Kathy Rinaldi’s obsession with pin trading: “She was like dealing, wheeling — like a drug deal.”

[43:21] Olympic History Fun Facts & Quirks

• Art, Sculpting & Naked Games: Jenny quizzes the group with obscure Olympic trivia (e.g., 1915 art competitions, nude competition in ancient Greece, barefoot marathon champions).
  • Jenny: “I do watch Bob Ross. So, happy trees—maybe if they're doing happy trees, I’m all in.”
• Iconic/Memorable Feats: Stories of super-aged competitors, runs of bad luck, and McDonald’s free burger pandemonium during the LA Games.

[49:13] Winter Olympics Recap & Standouts

• USA Men’s Hockey Gold: Pegula is fired up about Team USA’s first gold vs. Canada since 1980.
  • Quote – Jessica Pegula (50:27):
    “The freaking hockey winning gold medal insanity...I’m ready to, like, jump through a wall.”
• Pop Culture Tie-in:
  “Jack Hughes...scored the game winner...he dates Tate McRae.” (Pegula brings in both hockey and singer-dancer trivia.)
• Inspirational Athletes: The team celebrates stories of competitors from non-traditional nations, athletes with “normal jobs” (dentists, ER doctors), and widespread “Olympian” awe.
  • Madison: “Everyone has such an appreciation for every athlete that’s made it that far...it’s a huge feat to even call yourself an Olympian.”

[56:16] Who Am I? Tennis Trivia Game

• Last Week’s Answer Reveal: John Isner (most career aces, three kids, still involved in tennis); Jenny incorrectly guesses Ivo Karlovic.
• New “Who am I?” (Jessica): “Won a medal at the Olympics, wore lavender during a very important moment, six more titles than anyone in my family.” Fan guessing encouraged.

[58:08] Fan Q&A: Tournament Withdrawals Explained

• Question: What’s the process of withdrawing from a tournament? Are there fines, point losses, injury proof needed?
• Answer (Madison):
  • Each player is allowed two withdrawals per year without fine, but “zeroes” (no points) still apply to mandatory events. If you go over the limit, fines increase by rank and withdrawal number.
  • Continuous injury withdrawals are possible, but only as long as you skip consecutive tournaments.
  • On-site withdrawals allowed twice annually (with variations).
  • Madison: “It’s a lot of money” if you go over; Pegula: “Not easy to keep track of!”

Notable Quotes

• Jessica Pegula (on social media blunder, 08:03)
  “Thank you for giving me the waist of my dreams. But, like, what happened here?”
• Madison Keys (on Olympic heartbreak, 35:36)
  “I just want to go walk into the ocean now.”
• Desirae Krawczyk (on meeting famous athletes, 31:41)
  “We took a selfie with LeBron James. Did not see that in my Olympic debut.”
• Jenny Brady (on being star-struck, 32:59)
  “I see Yao Ming. Tommy, look! It’s Yao Ming. We have to get a picture...He’s massive!”
• Madison Keys (on village camaraderie, 40:03)
  “Everyone has such an appreciation for every athlete that’s made it that far, just because it’s a huge feat to even call yourself an Olympian.”

Memorable Moments

• Jenny’s car gaffe in Austin; Jess’s viral “snatched waist” mishap
• Olympic crowd chaos, medals vs. certificates, and Pin-trading drama (“Kathy Rinaldi, pin dealer supreme”)
• Jessica geeking out over hockey, linking Olympic overtime heroics to pop culture
• The “Who Am I?” tennis trivia and the lighthearted ribbing among the co-hosts

Timestamps for Major Segments

• [01:11] Dubai Winner Recap, Birthday Chat
• [04:01] Unforced Errors of the Week
• [17:32] Dubai Withdrawals/ Tour Schedule
• [21:47] Dubai Doubles + Austin Reports
• [28:10] Olympic Games Memories
• [38:12] The Olympic Village Experience
• [43:21] Olympic History & Trivia
• [49:13] Winter Olympics Stories & Recap
• [56:16] Who Am I? Segment
• [58:08] Fan Question: Withdrawal Rules

Overall Tone & Vibe

Upbeat, fun, and candid—with plenty of back-and-forth teasing, self-deprecating humor, and honest glimpses into both tennis and Olympic life. The episode is a blend of technical insight, genuine friendship, and quirky personal stories—a true “all-access pass” for fans wanting to peek behind the baseline.